Hydrochloric Acid → HCID 22185235, compound

HRID 1168720Notes

Reaction equation

HRID 1168720 reaction equation
[CH:1]1[CH:2]=[CH:3][C:4]2[NH:13][C:12]3[CH:11]=[N:10][CH:9]=[CH:8][C:7]=3[C:5]=2[CH:6]=1.[ClH:14].[Cl:15]N1C(=O)CCC1=O>O>[Cl:14][C:2]1[CH:3]=[C:4]2[C:5]([C:7]3[CH:8]=[CH:9][N:10]=[CH:11][C:12]=3[N:13]2[Cl:15])=[CH:6][CH:1]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 31398ChlorosuccinimideHCID 64961Beta-Carboline

Product 1

HCID 22185235HCID 22185235, compoundYield 20.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a suspension of norharmane (84 mg, 0.50 mmol) in water (3 ml) at RT was added 1M aqueous HCl (1.1 ml, 1.1 mmol). To this homogenous solution was added N-chlorosuccinimide (747 mg, 5.58 mmol) portionwise and the resulting solution was stirred at 60° C. to 70° C. for 3 h. The reaction was partitioned in EtOAc and saturated aqueous NaHCO3 and the organic layer was dried (brine; MgSO4) and then concentrated. The residue was chromatographed (2:3 THF-hexane) on silica gel to give 24 mg of 7,9-dichloro-β-carboline after triturating with (1:1) methylene chloride-hexane, then with hexane.

Workup

  1. customThe reaction was partitioned in EtOAc
  2. dry with materialsaturated aqueous NaHCO3 and the organic layer was dried (brine; MgSO4)
  3. concentrationconcentrated
  4. customThe residue was chromatographed (2:3 THF-hexane) on silica gel

Sources & evidence

ORD record
ord-df2601251c2148949ea5f571403b5b3f
Source dataset
uspto-grants-2003_09
Patent number
US06627637B2

Reaction notes

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